Ammonium formate → cis-(3-Methoxy-tetrahydro-pyran-4-yl)-methyl-amine

A slurry of 3-methoxy-tetrahydro-pyran-4-one (0.4 g, 3 mmol-described in WO03/093266(A1)), ammonium formate (1.9 g, 30 mmol), 10% palladium on charcoal (1 g) in water:MeOH (1:5, 6 ml) was stirred overnight after which time it was filtered through Hyflo, the mixture concentrated to remove the MeOH, the residue taken up in Et2O, dried (Na2SO4) and concentrated to afford the title product (0.2 g, 49%) as a yellow oil (contaminated by 10-20% of the trans isomer). 1H NMR (300 MHz, CDCl3) (cis isomer) δ 1.60-1.80 (2H, m), 2.95-3.00 (1H, m), 3.22-3.43 (5H, m). 3.82-3.95 (1H, m), 4.01-4.13 (1H, m).

1. filtrationwas filtered through Hyflo
2. concentrationthe mixture concentrated
3. customto remove the MeOH
4. dry with materialdried (Na2SO4)
5. concentrationconcentrated

ORD record

ord-2eb6a603fa684f3499509ee92512c2cb

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977358B2